Constantine Falkland Cary Smythe, MC (February 1, 1895 – November 18, 1980) was a Canadian businessman, soldier and sportsman in ice hockey and horse racing. He is best known as the principal owner of the Toronto Maple Leafs of the National Hockey League (NHL) from 1927 to 1961 and as the builder of Maple Leaf Gardens. As owner of the Leafs during numerous championship years, his name appears on the Stanley Cup eight times: 1932, 1942, 1945, 1947, 1948, 1949, 1951 and 1962.

Smythe is also known for having served in both World Wars, organizing his own artillery battery in the Second World War. The horses of Smythe's racing stable won the Queen's Plate twice among 145 stakes race wins during his lifetime. Smythe started and ran a successful sand and gravel business. He was a big supporter of the Ontario Society for Crippled Children and the Variety Club and founded the Conn Smythe Foundation philanthropic organization.

Conn Smythe was born on February 1, 1895, in Toronto to Albert Smythe, an Irish Protestant from County Antrim who immigrated to Canada in 1889, and Mary Adelaide Constantine, an English woman. Mary and Albert were married in the 1880s while immigrating to Canada. Albert and Mary had a rocky marriage and did not live together for more than a few months at a time.[1] Mary, who was known as Polly, was remembered by Conn as pretty, a drinker and troublemaker, while Albert was quiet, a vegetarian and a devoted member of Madame Blavatsky'sTheosophical movement.[2] Albert Smythe was a charter member of the Theosophical Society of Canada in 1891, and edited its newsletter until the final years of his life.

Smythe's first home was 51 McMillan Street, now known as Mutual Street, not far from the future site of Maple Leaf Gardens.[3] He was the second of two children born to Mary and Albert. Conn had a sister, Mary, five years older, who died due to illness in 1903. The family was poor and moved several times during Smythe's youth, the size of lodgings depending on Albert Smythe's wages at the time. At one point, Albert and Conn moved to a house in Scarborough while Mary and Polly stayed on North Street. Conn's mother Mary died in 1906, and Smythe attributes his mother's drinking with making him a lifelong abstainer from alcohol.[4] At age eleven Conn was christened and that was the first time that he insisted on Conn instead of his given name of Constantine.[4] Albert and Conn became estranged after Albert began a new relationship with Jane Henderson. The two married in 1913 and had a daughter Moira.[5]

Smythe first went to high school at Upper Canada College. He hated it, and after a year and a half he transferred to Jarvis Collegiate Institute.[6] Smythe developed his athleticism there, playing on hockey, rugby football and basketball teams, playing on city championship teams in basketball and hockey in 1912.[7] At the age of 16, Conn Smythe met Irene Sands, his future wife, after a football game against Parkdale Collegiate Institute, which she attended.[8] Albert Smythe wanted his son to attend university after grade 12 but Smythe defied his father, bolting at age 17 to become a homesteader on 150 acres (61 ha) in Clute Township, near Cochrane, Ontario.[9] After one summer building a home on the property only to have it destroyed by a devastating fire, Smythe changed his mind about living in the bush and he enrolled in engineering studies at the University of Toronto in the fall of 1912.[9] There he played hockey as a centre, captaining the Varsity Blues men's ice hockey team to the finals of the 1914 Ontario Hockey Association (OHA) junior championships and to the OHA junior championship the following year.[10] The coach of the losing team in 1915 was Frank J. Selke,[11] who years later would work for Smythe at Maple Leaf Gardens. Smythe also played on the University of Toronto football team, although not as a starter.

The First World War interrupted his studies. A week after winning the OHA championship in March 1915, Smythe and his eight teammates enlisted. Smythe recalled in his memoirs that he and several classmates tried to enlist at the beginning of the 1914–15 season, but were told to come back when they had beards.[12] After securing a provisional rank of lieutenant with the 2nd (Ottawa) Battery, 8th Brigade, on July 17, he headed to the Royal School of Artillery in Kingston, Ontario, in August for five weeks of training. He made full lieutenant on September 11, and was able to get himself transferred to the 40th (Sportsmen's) Battery of Hamilton, organized by publishing figure Gordon Southam, son of William Southam.[13] The unit, with Smythe as team manager, organized a team to compete in the OHA's senior league; they were one of four Toronto-based teams in the league in 1916. He played one game at centre, and then decided to replace himself with a better player.[14] The team did not complete the season, as the 40th Battery went overseas in February 1916.[15]

The Battery was ordered into the Ypres salient. On October 12, shelling found their position killing Major Southam and Sergeant-Major Norm Harvie, making Smythe temporarily commander of the Battery. The Battery fought for nearly two months in the trenches near the Somme before being relieved. In February 1917, Smythe earned a Military Cross, when during an attack the Germans counter-attacked with grenades. Smythe ran into the fight and killed three Germans and helped several wounded Canadian soldiers back to safety[16] On March 5, 1917, Smythe was awarded the Military Cross for "dispersing an enemy party at a critical time. Himself accounted for three of the enemy with his revolver."[17] After an attack where several Canadians were killed because of what Smythe thought was poor planning by the Battery's Major, Smythe wanted out.[18] Smythe transferred to the Royal Flying Corps in July 1917. One of his instructors was Billy Barker, who would later become the first president of the Toronto Maple Leafs.[19] Smythe served as an airborne observer, directing artillery fire. Smythe was shot down by the Germans and captured on October 14, 1917. He was imprisoned by the Germans at Schweidnitz (Swidnica) in Upper Silesia. He made two failed escape attempts and ended up in solitary confinement as a result. He was a POW until the end of the war.[20] Smythe would later make light of his fourteen months in captivity "We played so damned much bridge that I never played the game again."[21]

Following the war, Smythe returned to Toronto. With his accrued Army salary and the proceeds from the sale of his homestead plot, he started a sand and gravel business. For a while, the business became a partnership with Frank Angotti, who owned a paving business. To support the need for sand and gravel, Smythe bought land northwest of Toronto for a sand pit. He returned to the University of Toronto and finished his civil engineering degree in 1920. Irene and Conn were married during the school year. Smythe and his paving business partner split, and Smythe retained the sand and gravel business. The company was named C. Smythe Limited and the company slogan was "C. Smythe for sand", which he had painted on his trucks, the lettering in white on the blue of the trucks. Frank Selke, who had moved to Toronto, was one of Smythe's first employees in the business. Irene took sand and gravel orders over the phone as well as taking care of newborn son Stafford.[22] Smythe would own the business until 1961.[23]

In the evenings, he coached the University of Toronto varsity team. It was through his coaching of this team that he became involved in the NHL. The team traveled regularly to the Boston area for games against colleges from that area, with great success.[24] In 1926, Boston Bruins owner Charles Adams recommended him to Col. John S. Hammond, representing the owners of the new New York Rangers franchise, who was looking for someone to build his team. Smythe was hired to recruit a team, which he would then manage.[24] But on October 27, 1926, before the Rangers had played a regular season game, Hammond fired Smythe in favour of Lester Patrick. Smythe believed that he lost his job by refusing to sign two-time NHL scoring champion Babe Dye, against Hammond's wishes. Smythe thought Dye was not a team player.[25]

Smythe applied to coach the Toronto St. Pats, but was rejected in favour of Mike Rodden. He continued to coach for the University of Toronto and took on a new senior team made up of University of Toronto players, called the Varsity Grads. The team won the Allan Cup, and represented Canada at the 1928 Winter Olympics in St. Moritz the following year. Smythe refused to go when two Varsity Blues players he had promised could be part of the team were blocked by what he described as a "pressure play" from two Grads players to get relatives placed on the team instead. One of the players was Joe Sullivan, who years later became a Canadian Senator.[26]

Although no longer a Rangers employee, Smythe was invited to the Rangers' opening game in Madison Square Garden by Tex Rickard, an invitation he nearly turned down because he had felt the Rangers had short-changed him. Hammond paid Smythe $7,500 to settle his contract, and Smythe felt he was owed $10,000. At the insistence of his wife Irene, they traveled to New York and attended the opener in Rickard's private box. When the Rangers won the game, surprising the Montreal Maroons, Rickard offered Smythe a vice-presidency with the club. Smythe turned the Rangers down, partly because of the disputed $2,500, although Rickard ordered Hammond to pay off the rest. On the return trip to Toronto, Conn and Irene visited Montreal, where Smythe bet the $2,500 on a football game between Toronto and McGill. He then bet the $5,000 he won on the Rangers to defeat the St. Pats in Toronto, winning again, turning the $2,500 into $10,000 in three days.[27] The Rangers won the Stanley Cup in 1928, their second year of existence, largely with the players Smythe had brought to the team.

The Rangers went to the top of their division, while the St. Pats were doing poorly. J. P. Bickell, a part-owner of the St. Pats, contacted Smythe about becoming coach of the St. Pats. However, Smythe told Bickell that he was more interested in buying the team, or at least a stake in the team. Not long after, the St. Pats were put up for sale, and agreed in principle to be sold for $200,000 to a group who would move the team to Philadelphia. Bickell contacted Smythe and told him that if Smythe could raise $160,000 and keep the team in Toronto, Bickell would not sell his $40,000 interest. After persuading majority owner Charlie Querrie that civic pride was more important than money, Smythe put together a syndicate that included Bickell and several other investors that bought the St. Pats. Smythe himself invested $10,000 of his own money. Soon after the sale closed on February 14, 1927, the new owners changed the St. Pats' name to the Toronto Maple Leafs.[28]

At first, Smythe's name was kept in the background. However, when the Leafs promoted a public share offering to raise capital, they announced that "one of the most prominent hockey coaches in Toronto" would be taking over management of the club.[29] That prominent coach turned out to be Smythe. He succeeded Querrie as the team's governor, and installed himself as general manager. He installed Alex Romeril as coach.[30] For the next season (1927–28), Smythe changed the team's colours from green and white to their present blue and white. According to the Maple Leafs, the blue represents the Canadian skies, while white represents snow.[31] They were also the same colours as those of his sand and gravel business trucks.[32] Smythe also took over as coach and for the next three years served as team governor, general manager and coach.

Smythe developed a public image as a "red-faced, pepper-pot" with nicknames such as "little corporal" or "little dictator."[33] Smythe was not reluctant to chase players and referees on the rink and off.[33] Smythe also developed feuds with opposing coaches and general managers. He used any tactic available to disrupt the opponent. He advertised in a Boston newspaper inviting people to watch "a real hockey team, the Toronto Maple Leafs."[34] After learning that Boston general manager Art Ross suffered from hemorrhoids, he gave Ross a bouquet of flowers with a note in Latin describing where he should shove the flowers.[34]

Original Maple Leaf Gardens architectural depiction

In 1929, Smythe decided, in the midst of the Great Depression, that the Maple Leafs needed a new arena. The Arena Gardens seated 8,000 and the Maple Leafs were regularly filling it with 9,000 customers. Smythe knew it would take over a million dollars to construct and he got backing from the Sun Life insurance company for half a million.[35] He found a site owned by the T. Eaton Co. department store chain on Carlton Street, a site Smythe selected because it was on the street car line. Smythe gave up the coaching position to concentrate on the arena project. The building started construction on June 1, 1931, and was ready on November 12, 1931, after five months. As part of a corporate reorganization, Maple Leaf Gardens Ltd. was founded that year to own both the team and the arena. To pay for the building construction, the construction workers were paid with Maple Leaf Gardens stock instead of 20% of their pay. Selke, who had union connections, and Smythe were successful in negotiating the payment method in exchange for using unionized workers.[36]

In its first season in the new building, Smythe fired coach Art Duncan after five games and hired Dick Irvin to coach. Irvin promptly led the Maple Leafs to their first Stanley Cup as the Maple Leafs, and the franchise's third overall. While the Leafs would go to the finals every year except for 1934 and 1937 during Irvin's nine-year tenure, they were unable to win another Cup. By 1940, Smythe believed that Irvin had taken the Leafs as far as he could, and decided to replace him with former Leafs captain Hap Day, who had retired. Smythe also knew that he would be away in the war and felt that Irvin would not be tough enough without Smythe to back him up.[37] Meanwhile, the Montreal Canadiens had had a ten-win season, and were looking for a new coach. At the suggestion of Smythe, Irvin became the new coach of the Canadiens.[38]

Smythe first became interested in horse racing as a boy, when he would take stories his father wrote at the track to the newspaper office downtown. Smythe started owning horses in the late 1920s, but he rarely had any success. One early purchase turned out to be one of his most famous. When Mrs. L. A. Livingston sold off her stable, he bought Rare Jewel, a filly, for $250.[39] The filly regularly ran last. The horse was eligible for the Coronation Futurity Stakes, one of the best two-year-old races. Smythe was full of blind hope, and on the trainer's advice, entered her in the race. The day of the race, both the trainer and his partner gave the horse some brandy, unknown to Smythe, who bet over $100 on Rare Jewel. She won the race, a 100–1 longshot paying $214.40 on a $2 bet, besting future Queen's Plate winner Froth Blower. Between the winnings from his bets and his portion of the winner's purse as horse owner, Smythe won more than $10,000 on that one race.[40] Three weeks later, he put his windfall to work for the Maple Leafs by purchasing star defenceman King Clancy from the depression-strapped Ottawa Senators for $35,000. The purchase was only possible because of his gambling winnings, as the other Maple Leafs owners refused to pay the Senators' then-high price, and only agreed when Smythe volunteered to use his own money.[41]

Smythe continued to own horses through the 1930s, but he sold them in 1940, when he made plans to fight in the Second World War. He did not re-enter the racing business until 1954. In 1951, Smythe bought land for a farm in Caledon, Ontario, originally looking for a new location for a gravel pit. At first he kept only cattle, but in 1954 he decided to get back into owning race horses, in partnership with Larkin Maloney,[42] and an area was set aside to keep horses. Smythe learned about the business and went into breeding, buying mares in foal from top thoroughbred lines, and hiring future Hall of Fame trainer Yonnie Starr.[43]

Maloney and Smythe's most famous horse Wonder Where, also led to the breakup of the partnership. Wonder Where, named by Maloney, was bred at Frank Selke's farm in Quebec and bought by Maloney and Smythe in 1957. In 1959, Wonder Where had an outstanding season, including winning the Canadian Oaks. The horse was voted Canadian Horse of the Year for the year and later, the filly was inducted in the Canadian Horse Racing Hall of Fame. The Wonder Where Stakes was established in honour of the horse in 1965, becoming one of the Canadian Triple Tiara races for fillies in Canada in 1995. After the outstanding year in 1959, Maloney wanted to continue racing Wonder Where and Smythe did not, concerned over some tendon trouble. The horse broke down in a race in Fort Erie, and the partnership dissolved after that.[44]

While not the largest operation, Smythe's horses won 145 stakes races during his lifetime, a record second only to E. P. Taylor in Canada.[45] Smythe's stable won the Queen's Plate twice, the first in 1958 with Caledon Beau and the second in 1967 with Jammed Lovely.[46] In 1973, Smythe became a founding member of the Jockey Club of Canada. In 1977 he was inducted in the Canadian Horse Racing Hall of Fame. After his death, the Smythe stable was sold in 1981 to Gardiner Farms and Harlequin Ranches, for an estimated $2.5 million. Smythe's will gave the racing stable to the Conn Smythe Foundation, which as a charitable foundation, could not run a business. The new owners leased back the farm and stables. The only horse not in the sale was Jammed Lucky, Smythe's favourite, which was given to Smythe's grandson Tommy.[47]Jammed Lucky was 23 years old and had sired 25 winning foals to that point.[48]

In the Second World War, at age 45, Smythe again served in the Canadian Army. Initially, he was a captain in charge of a troop within the Canadian Officers Training Corps, based at the University of Toronto.[49] In 1941, along with Colonel Richard Greer, he formed the 30th Battery, a sportsmen's anti-aircraft battery that was part of the 7th Toronto Regiment, Royal Canadian Artillery, Canadian Active Army.[50] Smythe was made acting major and Officer Commanding. He was offered a higher rank to become the army's sports officer, but turned it down.[37] After first serving on Vancouver Island to defend against Japanese attack, the Battery embarked in September 1942 to England.[51] After being stationed in England for nearly two years, Smythe and his unit were sent to France in July 1944, where within three weeks he was badly wounded when the Germans bombed an ammunition depot.[52] For the rest of his life he would walk with a limp and suffer bowel and urinary tract problems. He was sent back to Canada in September on a hospital ship.

Smythe, who had seen that the army was using improperly trained troops due to a lack of soldiers, interviewed other soldiers during his time in the hospital, compiling a record over which to confront Mackenzie King. King had developed an official government policy of voluntary service for political reasons and Smythe saw the detrimental effect it had on the Army. Volunteers tried to press home service troops into active service to assist and augment the undermanned troops overseas.[53] From his bed in the Chorley Park Hospital, Smythe dictated a statement to The Globe and Mail newspaper, which printed it on its front page on September 19, 1944:

Smythe's statement, which provoked a political crisis in Canada

“

The need for trained reinforcement in the Canadian Army is urgent.

During my time in France and in the hospitals of France and England, I was able to discuss the reinforcement situation with officers of units representing every section of Canada. I talked to officers from far Eastern Canada, French Canada, Ontario and all the Western Provinces. They agreed that the reinforcements received now are green, inexperienced and poorly trained. Besides this general statement, specific charges are that many have never thrown a grenade.

Practically all have little or no knowledge of the Bren gun and finally, most of them have never seen a Piat anti-tank gun, let alone fired one. These officers are unaniminous in stating that large numbers of unnecessary casualties result from this greenness, both to the rookies and to the other soldiers, who have the added task of trying to look after the newcomers as well as themselves.

I give these true facts of the reinforcement situation in the hope that:

Col Ralston, if he has other information, will know that his facts are out of date or that he has been misinformed;

The taxpayer will insist that no more money be spent on well-trained soldiers in this country except to send them to the battle fronts;

The people who voted these men should be used overseas when needeed should insist on the Government carrying out the will of the people; and

The relatives of the lads in the fighting zones should ensure no further casualties are caused to their own flesh and blood by the failure to send overseas reinforcements now available in large numbers in Canada.

Smythe was accused of acting solely for political gain. The publisher of the Globe and Mail at the time was prominent Conservative George McCullagh, and Smythe was friends with Ontario Conservative Premier George Drew.[55] McCullagh and Drew may have used Smythe for their political ends to defeat King.[56] The issue of lack of reinforcements was well-known within the Army and Smythe did not make any complaints to senior officers while in active service.[56] Despite being criticized, Smythe kept up his public criticism in the newspapers. After James Ralston, Canada's defence minister, traveled to Italy, he saw for himself the shortage of skilled reinforcements. Ralston, who King did not trust, was replaced with Andrew McNaughton, who was against conscription. However, even King saw the need to send troops for the Canadian Army and he ordered 17,500 reserve troops to Europe in November 1944, which started to arrive in January 1945[57]

While Smythe was away, a committee, headed by Ed Bickle, Bill MacBrien, and Selke ran Maple Leaf Gardens Ltd. Upon his return from the military, Smythe found himself in the middle of a power struggle over the presidency of Maple Leaf Gardens Ltd. Smythe suspected that MacBrien, a member of the board of directors, wanted to succeed Bickle as president and give Smythe's job to Selke, who had been acting general manager in Smythe's absence. Smythe wanted to be president and asked Selke for his support. Selke equivocated, and relationship between the two long-time friends turned acrimonious, leading to Selke's resignation in May 1946.[58][59] Two months later, Selke became head of hockey operations for the Montreal Canadiens and manager of the Montreal Forum, succeeding Tommy Gorman.[59]

With the support of J. P. Bickell and with the help of a $300,000 loan from Toronto stockbroker and Gardens shareholder Percy Gardiner, Smythe was able to buy enough stock to become majority shareholder of Maple Leaf Gardens Ltd. He was thus able to install himself as president of the Gardens on November 19, 1947.[60][61][62] Andy Lytle, sports editor of the Toronto Star, said the appointment "simply makes official what he has been for years in actuality ... Smythe and the Gardens are synonymous terms."[63] MacBrien was made chairman. Smythe repaid his debt to Gardiner by 1960.[64] He later succeeded MacBrien as chairman of the board.

Smythe oversaw one of hockey's greatest dynasties when Toronto won six Stanley Cups in 10 seasons between 1942 and 1951. Hap Day coached the team to five of those Cups and was assistant general manager for the sixth. He was named in a poll of Canadian sports editors the "most dominating personality in any capacity in sports" for 1949. The Maple Leafs were masters of playoff hockey; their regular-season performances were usually fair to good or just good enough to make the playoffs.[65] Smythe was known for caring little about gaudy regular season records but he did care about winning the Cup, because "winning sells tickets."[66]

However, the Leafs spent most of the 1950s as a mediocre team, struggling under three different coaches while Day remained assistant general manager under Smythe. Even so, in 1955, Smythe turned over most responsibility for hockey operations to Day, but nominally remained general manager.[67] However, just after the Leafs were eliminated from the playoffs in 1957, Smythe told the media that it had been "a season of failure" and that he did not know if the 55-year-old Day would be available for the next season. Day felt that his legs had been cut out from under him and resigned.[68]

By this time Smythe had turned the operation of the hockey team over to a seven-person committee, headed by his son, Stafford Smythe. Newspaper owner John Bassett was another member of the committee, as was Percy Gardiner's son, George Gardiner. The committee became known as the "Silver Seven" because the seven had been "born with a silver spoon in their mouths."[69] Initially, all members were in their 30s or early 40s, but that changed before the end of the year when 54-year-old Harold Ballard, president of the Toronto Marlboros, was appointed to the committee to fill a vacancy. The committee hired Punch Imlach as general manager, who would later take over the coaching job.[70]

Smythe was an NHL owner during the era before the player's union. The NHL was only six teams and players who didn't toe the line could easily be demoted to the minor leagues and a replacement found. Players who didn't follow Smythe's rules were traded or sent to the minors. Two players, Danny Lewicki and John McCormack were both demoted to the minors for getting married without Smythe's permission.[71]

“

The rules are simple. Aside from what you wear, what you say, what you eat, what you drink, who you're with, where you're going, how much you weigh and what you think, the club has little, if any, interest in the hired help, outside working hours. There's one thing about it: the pay is good and it's always on time. There's more civil liberty in digging a ditch. But most of these guys are in a rut. They still seem to prefer hockey.

While the pay was relatively good, it still left many players looking for other jobs during the off-season, while the owners were all wealthy men.[73] The conditions led to two organizing efforts at forming a player's union, which Smythe was vehemently against.[74] From 1957 onwards, Smythe, along with other NHL owners including James D. Norris of the Chicago Black Hawks and his half brother Bruce Norris of the Detroit Red Wings were accused of union busting activities related to the attempt by Ted Lindsay and a group of NHL players to form an NHL Players Association. Mr. Smythe's role in those affairs are dramatized in the movie, Net Worth. Jimmy Thomson, who was acting captain of the Maple Leafs when the players started to organize[75] was singled out by Smythe. Smythe detailed all the monies Thomson had been paid by the organization going back to junior, while he arranged for Thomson to be left off the team, allegedly calling Thomson a traitor and publicly blaming him for the team's poor season. Thomson finally announced to the press that he would never play again for the Maple Leafs.[76] Thomson and Tod Sloan were traded away to Chicago.[77] The NHL owners eventually agreed to make some concessions to the players, such as contributing to the players' pensions.[77] The owners were able to temporarily head off the formation of the union, although it would eventually be organized some ten years later.

Though the committee made most decisions involving the Leafs, Smythe was not a hands-off owner and was constantly fighting with his son. Stafford commented: "My father has always given me lots of rope. When I was thirty, I was ten years ahead of everybody. But at forty, I'm ten years behind everybody." Finally, in 1961, Stafford resigned from the Silver Seven and this spurred Conn.[78] After four years of fighting, he offered to sell his shares to Stafford and in November 1961, Smythe sold 45,000 of his 50,000 shares in Maple Leaf Gardens Ltd. to a partnership of his son, Ballard, and Bassett for $2.3 million—a handsome return on his investment of 34 years earlier.[79] At first, Smythe thought the sale was only to his son, and when he learned that it was to the threesome, he was furious with Stafford. He had hoped that Stafford would eventually keep the Gardens for his son Tommy. Despite his misgivings, Smythe did not cancel the deal.[80]

As part of the deal, Smythe resigned as president and managing director, nominating Stafford to succeed him. On Stafford's instigation, the board then granted Smythe a $15,000 annual allowance, an office at the Gardens, and a car and driver for the rest of his life. Stafford, Ballard and Bassett then nominated Smythe as chairman of the board.[81] Smythe retired as NHL governor on February 5, 1962, a position he had held since 1927.[82] Smythe resigned the chairmanship after Toronto won the Stanley Cup in 1962 and Bassett succeeded him.

In 1964, Smythe opposed the Lester Pearson government's plan to replace the traditional Canadian flag with a completely new design. He wrote to Pearson, whom he had known since the 1920s: "In the Olympic Games, the whole world is represented and when Canada sometimes wins a Gold Medal everybody knows, when the Red Ensign (see Canadian Red Ensign) is raised to the masthead, that Canada has won."[83] Smythe disagreed that a new flag would help to unify the country. Smythe switched his support to John Diefenbaker. Smythe wrote over 300 letters to Members of Parliament.[84] In 1965, he unsuccessfully lobbied for the Red Ensign to be flown at the Gardens instead of the new Flag of Canada. Harold Ballard ordered the new flag flown because calls were more than three to one in favour of the new flag.[85]

In March 1966, Smythe sold his remaining shares and resigned from the board of directors after a Muhammad Ali boxing match was scheduled for the Gardens. He found Ali's refusal to serve in the U.S. Army in the Vietnam War to be offensive, because, as he put it in his autobiography "The Gardens was founded by men – sportsmen – who fought for their country. It is no place for those want to evade conscription in their own country. The Gardens was built for many things, but not for picking up things that no one else wants."[86] He also said that by accepting the fight, Gardens owners had "put cash ahead of class."[87]

Smythe stayed away from the Gardens and he took pot shots in the press, stating that he had been "traded for $35,000 and a black Muslim minister."[88] The seats at the Gardens had been replaced with new, narrower ones and Smythe commented that "only a slim, young man could sit in them but the prices are so high that only a fat rich man could afford them."[88]

Smythe continued to be sought out for his views on hockey. When the NHL expanded to 12 teams from six in 1967, he openly opposed the expansion on the basis that it would make for inferior hockey. "We had the best players in the world split between six teams, and hockey was always worth the money."[89]

By this time Conn and Stafford were not on speaking terms and it fell to Tom Smythe, Stafford's son, to mediate between the two. Stafford built a new office suite at the Gardens for Conn, and the feud was over.[90] After Stafford was charged in 1971 with fraud and became ill with a stomach ulcer, Conn was with him in hospital when he died. According to Conn, Stafford's last words to him were "see dad, I told you they wouldn't put me in jail."[91]

After the Second World War, Smythe became involved in charities and would remain so for the rest of his life. He became heavily involved in the Ontario Society for Crippled Children. Smythe helped organize the financing and construction of their Variety Club Village complex in Toronto.[92] In 1975, at the age of 80, Smythe organized the financing and building of the Ontario Community Centre for the Deaf, which opened in 1979.[93]

In 1960, after paying off his debt to Percy Gardiner, Smythe set up the Conn Smythe Charitable Foundation, which distributes money to charities in the Toronto area. The foundation was operated by Conn, his children and Hap Day. Day continued to help with the Foundation until his death in 1990. Before he died, Conn arranged for his grandson Thomas Smythe to continue the Foundation after his death.[94]

Smythe supervised the construction of the Hockey Hall of Fame building in Toronto in 1961. He served as the Hall's chairman for several years, but resigned in June 1971 when Busher Jackson was posthumously elected into the Hall. Smythe said that it made him sick to think of Jackson alongside such Leafs as "Apps, Primeau, Conacher, Clancy and Kennedy. If the standards are going to be lowered I'll get out as chairman of the board."[95] Jackson was notorious for his off-ice lifestyle of drinking and broken marriages.[96] Frank Selke, head of the selection committee defended the selection on the belief that a man should not be shut out "because of the amount of beer he drank."[97]

Smythe Park and Recreation Centre in Toronto is located on the site of his old gravel pit. The surrounding neighbourhood is named Rockcliffe-Smythe, partly a sub-division Smythe built for war veterans.[98] Smythe made provisions for a portion of the lands of the sub-division to be reserved for the centre. A street north of Eglinton Avenue, west of Markham Avenue, is named Conn Smythe Drive in his honour.[99]

His autobiography, Conn Smythe: If You Can't Beat 'Em in the Alley, written with Scott Young, was published posthumously in 1981. The title was taken from Smythe's credo, "If you can't beat 'em in the alley, you can't beat 'em on the ice."[100] In Smythe's memoir he describes it as the most misunderstood remark he ever made. Rather than meaning that his players should go out and bully the opposition, he meant the opposite; that his players should refuse to be bullied by the opposition.[100]

Smythe married Irene Sands on March 17, 1920, at Central Methodist Church. The couple lived in an apartment on St. Clair Avenue, then moved to the Runnymede area of Toronto to be close to Smythe's sand and gravel business, which operated a gravel pit north-west of Jane Street and St. Clair. (Smythe Park exists on the site today). In 1927, after their first two children, Stafford and Miriam, were born, they moved to the Baby Point enclave of Toronto, where they would live for the rest of their lives. Irene and Smythe had two other children, Hugh and Patricia. Hugh became a doctor; a specialist in rheumatology, and later a director of Maple Leaf Gardens. Patricia died due to an allergic attack at the age of ten, in 1945. Stafford became involved in the Smythe sand and gravel business and Maple Leaf Gardens before dying of complications from a bleeding ulcer in 1971. Stafford's son Thomas was a stick boy with the Maple Leafs and later was involved with the Toronto Marlboros and Doug Laurie Sporting Goods at Maple Leaf Gardens, before becoming director of the Smythe Charitable Foundation after Conn's death.

Smythe's father died in 1947 at 86 years of age. Smythe had had a rapprochement with his father, seeing him at Christmas and at times when Albert came to Toronto to preach.[102] After his father's death, Smythe joined the Theosophical Society and remained a member for life.[103] In 1977, Smythe explained why he was a theosophist: "It's because a theosophist teaches you that ya can't get away with anything in this life anyway."[104]

Irene Smythe was diagnosed with cancer after Christmas 1963. The illness progressed and Irene died on June 20, 1965. Due to the amount of pain Irene endured, Conn and Irene considered using a revolver to end her life, but near the end she told Conn that it was a "coward's way out" and she endured.[105] After the amount of pain Irene endured, Smythe called her death a "blessed release." Smythe set up a foundation at the University of Toronto in her name, which opened the Irene Eleanor Smythe Pain Clinic at Toronto General Hospital.[106][107]

On April 20, 1978, Smythe suffered a heart attack. He spent a month in the hospital, in time to spend May 18 at Woodbine, where he had four horses racing that day.[108] His health continued to deteriorate and Conn realized that he was dying. He arranged for Thomas Smythe to take over the Conn Smythe Foundation, and he made gifts of money to relatives. Conn Smythe died at the age of 85 in 1980 at his home on Baby Point.[109] He is interred with Irene at Park Lawn Cemetery in Toronto.